Method for making 1,1,3,3-tetrachloropropene

Abstract

A process for the manufacture of 1,1,3,3-tetrachloropropene, the process comprising dehydrochlorinating 1,1,1,3,3-pentachloropropane, where said step of dehydrochlorinating 1,1,1,3,3-pentachloropropane takes place in the presence of an oxidizing agent and in the presence of a Lewis acid, and where the oxidizing agent is chlorine and the Lewis acid is ferric chloride.

What is claimed is: 
     
       1. A process for the manufacture of 1,1,3,3-tetrachloropropene, the process comprising:
 dehydrochlorinating 1,1,1,3,3-pentachloropropane within a reaction mixture, where said step of dehydrochlorinating 1,1,1,3,3-pentachloropropane takes place in the presence of an oxidizing agent and in the presence of a Lewis acid, and where the oxidizing agent is chlorine and the Lewis acid is ferric chloride. 
 
     
     
       2. The process of  claim 1 , wherein said step of dehydrochlorinating takes place in the presence of from about 30 to about 10,000 ppm of the ferric chloride, based upon an overall weight of the reaction mixture. 
     
     
       3. The process of  claim 1 , wherein said step of dehydrochlorinating takes place in the presence of from about 100 ppm to about 3 wt % of the chlorine, based upon an overall weight of the reaction mixture. 
     
     
       4. The process of  claim 1 , wherein said step of dehydrochlorinating includes reactive distillation. 
     
     
       5. The process of  claim 1 , wherein said step of dehydrochlorinating takes place at a pressure of from about 0.05 atmospheres to about 0.5 atmospheres. 
     
     
       6. The process of  claim 1 , wherein said step of dehydrochlorinating takes place at a temperature of from about 60° C. to about 160° C. 
     
     
       7. The process of  claim 1 , wherein said step of dehydrochlorinating includes reactively distilling a crude 1,1,1,3,3-pentachloropropane stream. 
     
     
       8. The process of  claim 7 , wherein the crude 1,1,1,3,3-pentachloropropane stream includes 1,1,1,3,3-pentachloropropane, carbon tetrachloride, vinyl chloride, iron, and at least one of amines, nitriles, amides, and phosphates. 
     
     
       9. The process of  claim 1 , wherein said step of dehydrochlorinating includes reactively distilling a partially purified 1,1,1,3,3-pentachloropropane stream. 
     
     
       10. The process of  claim 9 , wherein said partially purified 1,1,1,3,3-pentachloropropane stream includes 1,1,1,3,3-pentachloropropane, carbon tetrachloride, and vinyl chloride. 
     
     
       11. The process of  claim 1 , further comprising a step of collecting the 1,1,3,3-tetrachloropropene as a product. 
     
     
       12. A process for the manufacture of 1,1,3,3-tetrachloropropene, the process comprising:
 (i) providing 1,1,1,3,3-pentachloropropane; chlorine, as an oxidizing agent; and ferric chloride, as a Lewis acid, in a mixture within a reaction vessel, and 
 (ii) reactively distilling the mixture within the reaction vessel to thereby dehydrochlorinate the 1,1,1,3,3-pentachloropropane to 1,1,3,3-tetrachloropropene and hydrogen chloride. 
 
     
     
       13. The process of  claim 12 , wherein the step of reactively distilling further includes removing the 1,1,3,3-tetrachloropropene and the hydrogen chloride from the reaction zone by distillation during the course of the reactively distilling step. 
     
     
       14. The process of  claim 13 , wherein the removing of the 1,1,3,3-tetrachloropropene and the hydrogen chloride occurs continuously during the course of the reactively distilling step.